Catalytic Asymmetric Transformations of Racemic Aziridines

被引：31
作者：
Chai, Zhuo [1 ]
机构：
[1] Anhui Normal Univ, MOE Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat, Inst Organ Chem,Coll Chem & Mat Sci, 189 South Jiuhua Rd, Wuhu 241002, Anhui, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 12期
基金：
中国国家自然科学基金;
关键词：
aziridine; ring opening; kinetic resolution; dynamic kinetic asymmetric transformation; asymmetric catalysis; 3+2 CYCLOADDITION; KINETIC RESOLUTION; VINYL AZIRIDINES; CONCISE SYNTHESIS; RAC-AZIRIDINES; ALKYLATION; SUBSTITUTION; REACTIVITY; ALDEHYDES; INDOLES;
D O I：
10.1055/s-0039-1690857
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.
引用
收藏
页码：1738 / 1750
页数：13
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共 67 条
  • [11] CeCl3 promoted asymmetric cycloaddition of isocyanates with 2-vinylaziridines
    Dong, C
    Alper, H
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (10) : 1537 - 1540
  • [12] Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes
    Fu, Gregory C.
    [J]. ACS CENTRAL SCIENCE, 2017, 3 (07) : 692 - 700
  • [13] Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents
    Ge, Chen
    Liu, Ren-Rong
    Gao, Jian-Rong
    Jia, Yi-Xia
    [J]. ORGANIC LETTERS, 2016, 18 (13) : 3122 - 3125
  • [14] Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes
    Hao, Wei
    Wu, Xiangyu
    Sun, James Z.
    Siu, Juno C.
    MacMillan, Samantha N.
    Lin, Song
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (35) : 12141 - 12144
  • [15] Nucleophilic ring opening of aziridines
    Hu, XE
    [J]. TETRAHEDRON, 2004, 60 (12) : 2701 - 2743
  • [16] The Chemistry of Transition Metals with Three-Membered Ring Heterocycles
    Huang, Chung-Yang
    Doyle, Abigail G.
    [J]. CHEMICAL REVIEWS, 2014, 114 (16) : 8153 - 8198
  • [17] Palladium(II)-Catalyzed Formal [3+2] Cycloaddition of Aziridines with 3-Substituted Indoles: Synthesis of Enantioenriched Pyrroloindolines
    Huang, You-ming
    Zheng, Chang-wu
    Pan, Lu
    Jin, Qiao-wen
    Zhao, Gang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 10710 - 10718
  • [18] Regiodivergent Ring-Opening Cross-Coupling of Vinyl Aziridines with Phosphorus Nucleophiles: Access to Phosphorus-Containing Amino Acid Derivatives
    Kang, Dahye
    Kim, Taehwan
    Lee, Hyunpyo
    Hong, Sungwoo
    [J]. ORGANIC LETTERS, 2018, 20 (23) : 7571 - 7575
  • [19] Insights on the Origin of Regiodivergence in the Parallel Kinetic Resolution of rac-Aziridines Using a Chiral Lanthanum-Yttrium Bimetallic Catalyst
    Kisan, Hemanta K.
    Sunoj, Raghavan B.
    [J]. ACS CATALYSIS, 2018, 8 (08): : 7633 - 7644
  • [20] Palladium-based kinetic resolution of racemic tosylaziridines
    Leung, WH
    Mak, WL
    Chan, EYY
    Lam, TCH
    Lee, WS
    Kwong, HL
    Yeung, LL
    [J]. SYNLETT, 2002, (10) : 1688 - 1690
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